Fluoroolefins represented by the formula: CF3(CX2)nCF═CH2, the formula: CF3(CX2)nCH═CHF (wherein X represents halogen), and the like are useful compounds as, for example, various functional materials, solvents, refrigerants, blowing agents, and monomers for functional polymers or starting materials of such monomers. In particular, of the fluoroolefins mentioned above, 2,3,3,3-tetrafluoropropene (hereinafter abbreviated as “HFO-1234yf”) represented by CF3CF═CH2 has gained attention because it offers promising prospects as a refrigerant compound of low global-warming potential.
The HFO-1234yf is known to be produced by a method comprising fluorinating a halopropane or halopropene used as a starting material by using hydrogen fluoride (HF), or by a method suitably combining hydrogenation and dehydrohalogenation. For example, as also disclosed in Patent Literature (PTL) 1, when 1,1,1,2,3,3-hexafluoropropene (HFO-1216) is used as a starting material, the HFO-1234yf is produced in accordance with the following reaction process:CF3CF═CF2+H2→CF3CFHCF2H (HFC-236ea)  (1)CF3CFHCF2H→CF3CF═CFH (HFO-1225ye(E/Z))+HF  (2)CF3CF═CFH+H2→CF3CFHCFH2 (HFC-245eb)  (3)CF3CFHCFH2→CF3CF═CH2 (HFO-1234yf)+HF  (4)
A reaction process is also known that comprises fluorinating HFO-1243zf to obtain HFC-245eb as in reaction formula (5) below, and conducting a reaction represented by reaction formula (4) above to obtain HFO-1234yf.CF3CH═CFH+F2→CF3CFHCFH2 (HFC-245eb)  (5)CF3CFHCFH2→CF3CF═CH2 (HFO-1234yf)+HF  (4)
Accordingly, in any reaction process, HFC-245eb is subjected to a dehydrofluorination reaction to produce HFO-1234yf. The dehydrofluorination reaction has been considered in various ways (see, for example, PTL 2 to PTL 4), and methods have been proposed for efficiently producing a fluorine-containing olefin, such as HFO-1234yf, by suitably adjusting the type of catalyst, reaction temperature, contact time, and the like.